(3-(3-Methoxy-3-oxopropyl)phenyl)boronic acid

Base Information

• Chemical Name: (3-(3-Methoxy-3-oxopropyl)phenyl)boronic acid
• CAS No.: 833472-82-5
• Molecular Formula: C10H13BO4
• Molecular Weight: 208.022
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID00407338
• Wikidata: Q82212587
• Mol file: 833472-82-5.mol

Synonyms:833472-82-5;(3-(3-Methoxy-3-oxopropyl)phenyl)boronic acid;3-(2-Methoxycarbonylethyl)phenylboronic acid;Methyl 3-(3-boronophenyl)propionate;[3-(3-methoxy-3-oxopropyl)phenyl]boronic acid;3-(3-methoxy-3-oxopropyl)phenylboronic acid;[3-(2-methoxycarbonylethyl)phenyl]boronic Acid;MFCD04115648;(3-(2-methoxycarbonylethyl)phenyl)boronic acid;SCHEMBL2562738;DTXSID00407338;IPXZIWCEVNDHFD-UHFFFAOYSA-N;AMY29853;AKOS015851606;AB20325;BS-24217;SY272098;CS-0131389;FT-0688803;3-(2-methoxycarbonylethyl)phenyl boronic acid;D81975;EN300-7390260;A864272;(4-Methyl-6,7-dihydro-4H-thieno[3,2-c]pyran-4-yl)aceticacid

Chemical Property of (3-(3-Methoxy-3-oxopropyl)phenyl)boronic acid

Chemical Property:

• Vapor Pressure: 3.58E-06mmHg at 25°C
• Melting Point: 96-100°C
• Refractive Index: 1.522
• Boiling Point: 371.4 °C at 760 mmHg
• PKA: 8.42±0.10(Predicted)
• Flash Point: 178.4 °C
• PSA: 66.76000
• Density: 1.18 g/cm³
• LogP: -0.52800
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: -
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 208.0906891
• Heavy Atom Count: 15
• Complexity: 208

Purity/Quality:

98%min ^*data from raw suppliers

3-(2-Methoxycarbonylethyl)phenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)CCC(=O)OC)(O)O
• Uses: 3-(2-Methoxycarbonylethyl)benzeneboronic acid is involved in the preparation of antimalarial and anticancer ethylenediamine inhibitors to protein farnesyltransferase.

Technology Process of (3-(3-Methoxy-3-oxopropyl)phenyl)boronic acid

There total 2 articles about (3-(3-Methoxy-3-oxopropyl)phenyl)boronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

methyl 3-(3'-bromophenyl)-propionate (151583-29-8) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 3-(2-methoxycarbonylethyl)phenylboronic acid, (833472-82-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; dimethyl sulfoxide; at 90 ℃; Inert atmosphere; Sealed tube;

Reference yield:

3-(3-bromophenyl)propanoic acid (42287-90-1) → 3-(2-methoxycarbonylethyl)phenylboronic acid, (833472-82-5)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 3 h / Reflux

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; dimethyl sulfoxide / 90 °C / Inert atmosphere; Sealed tube

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; thionyl chloride; potassium acetate; In 1,4-dioxane; dimethyl sulfoxide;

Reference yield: 70.0%

methyl 4-(3-bromophenyl)butanoate + 3-(2-methoxycarbonylethyl)phenylboronic acid, (833472-82-5) → tert-butyl 2-(5'-benzyl-2'-cyanobiphenyl-3-yloxy)acetate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In N,N-dimethyl-formamide; at 90 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.6b00188

upstream raw materials:

methyl 3-(3'-bromophenyl)-propionate

2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane

3-(3-bromophenyl)propanoic acid

Refernces